Wiring term for insulation failure due to compression. Google research 'wiring cold flow'
Wow, 30+ years in the business, this is the first time I have EVER heard of this. But then again, I've never done MIL SPEC work. I'm not doubting you, I see the references, it's just NEVER come up in my world before.
Looks like it can reduce the dielectric value of the insulation, but I really wonder how real this problem is. If you were using 600V rated wire at 600V, maybe. But if you are using 600V rated wire at 120V or even 480V? I doubt this is something to get my undies in a twist about.
Back to the strippers, if I am working in a production shop environment doing 20 or 30 terminations an hour, you bet I want an automatic stripper. I find the multi-wire free form strippers like the Radio Shack one preferrable to the Ideal ones because you don't have to worry about placing the wire in the right (or rather wrong) groove. But I also find that they don't last as long either, those little razor wires tent to dull pretty fast and then the tool is garbage, but those Ideal strippers seem to last a lot longer and even when dull, they still work, it just starts to take more effort and your hand gets tired. So if someone else is providing the tool, multi-wire. If I have to buy it, Ideal.
But for field work? I wouldn't be caught dead weilding one of those. Not only are they too bulky for a tool belt, I couldn't take the ridicule from those around me.